Best and worst in-season trades for each franchise over the last 20 years

ArizonaAtlantaBaltimoreBostonChicago Cubs
Chicago White Sox – CincinnatiClevelandColoradoDetroit
HoustonKansas City – LA AngelsLA DodgersMiami
MilwaukeeMinnesotaNew York Mets – New York YankeesOakland
PhiladelphiaPittsburghSt. LouisSan Diego – San Francisco
SeattleTampa BayTexasTorontoWashington

Bill Streicher-USA TODAY Sports
Philadelphia Phillies
Best trade: Acquired Cliff Lee and Ben Francisco from Indians for Carlos Carrasco, Jason Donald, Jason Knapp, and Lou Marson (July 29, 2009)
The devil is in the details here. While the Phillies wouldn’t really miss any of the four players they sent to Cleveland for Lee, this trade didn’t end up how the team wanted it to…because they traded Lee to Seattle less than five months later, only to sign him as a free agent following the 2010 season. In his first stint with the Phillies, Lee had a 3.39 ERA in 12 starts, striking out 74 and only walking seven. The three players they received when they dealt Lee to Seattle didn’t make much of an impact on the franchise, while Lee had a 3.18 ERA in 212 1/3 innings for the Mariners and Rangers in 2010, leading Texas to the AL pennant. But I’ve gone off track. Lee was great for the Phillies in 2009, and he was absolutely not the reason they fell to the Yankees in the World Series.

Worst trade: Acquired Tommy Joseph, Seth Rosin, and Nate Schierholtz from Giants for Hunter Pence (July 31, 2012)
The trade that brought Pence to Philadelphia from Houston is the one that gets most of the scorn when talking about the Phillies’ questionable midseason moves. But their trade of Pence to the Giants was arguably worse. Even though he still had a year and a half worth of control left when the Phillies dealt him, all they were able to acquire in return was a fourth outfielder (Schierholtz) and a pair of prospects in Rosin and Joseph. Schierholtz was non-tendered after the 2012 season. Rosin was taken by the Mets in this winter’s Rule 5 Draft. Joseph has played 91 games in the organization since the trade while dealing with a litany of injuries. That’s a pretty pathetic return for a guy like Pence, who the Phillies nearly emptied the farm for in 2011.


Pittsburgh Pirates
Best trade: Acquired Jason Bay, Oliver Perez, and Cory Stewart from Padres for Brian Giles (August 26, 2003)
Ah yes, the rare “trade that works out well for both sides”. Giles was a great player for Pittsburgh (after being acquired straight up for Ricardo Rincon), hitting .308/.426/.591 with 165 homers and making two All-Star teams in five years wearing the black and gold. The ever-thrifty Pirates dealt Giles to the Padres as a post-trade deadline waiver deal in 2003, and they were somehow able to get proper value in return for him. In six years with Pittsburgh, Bay hit .281/.375/.515 with 139 homers, a Rookie of the Year award, and two All-Star nods. before being spun off to the Red Sox in a three-team trade that didn’t end well for the Bucs. Perez had a career in Pittsburgh that could be best described as “erratic”, as he pitched to a 2.98 ERA in 196 innings in 2004, adding 239 strikeouts. But his skills declined rapidly after that, and he was dealt to the Mets for Xavier Nady (who was later traded to the Yankees as part of a package for Jose Tabata). Getting a few years of above average performance from two players is probably the biggest win you can think of for Pittsburgh, which says a lot in and of itself.

Worst trade: Acquired Matt Morris from Giants for Rajai Davis and Steve McFarland (July 31, 2007)
It was actually quite difficult to choose just one terrible trade for the Pirates – they’ve made some bad ones over the past 20 years. I went with the Morris trade, because even though they didn’t give up much value at all, it just didn’t make any sense.  When the Pirates acquired Morris in 2007, they were in last place in the NL Central, 20 games under .500. Naturally, that’s the perfect time to buy a starting pitcher who turns 33 in August, has a 4.35 ERA on the season, and is owed over $10 million in 2008. Predictably, this worked out terribly for the Pirates. Morris had a 7.04 ERA in 16 starts with Pittsburgh, and was released before the end of April 2008. He never pitched in pro baseball again. The incompetence is just mind-boggling.


St. Louis Cardinals
Best trade: Acquired Scott Rolen and Doug Nickle from Phillies for Placido Polanco, Bud Smith, and Mike Timlin (July 29, 2002)
The Cardinals actually gave up a player who would contribute some value to the Phillies – Polanco, who played very well in first three-year stint with the Phillies before getting dealt to the Tigers, and later coming back for three more, less successful years. The Cardinals also sent Smith, a promising young pitcher who didn’t throw an inning in the majors for Philadelphia, and Timlin, a journeyman reliever who left as a free agent that winter, to the Fightins in exchange for the disgruntled Scott Rolen. And boy, did Rolen ever produce with the Cardinals. In parts of six seasons with the team, he hit .286/.370/.510, making four All-Star teams and winning three Gold Gloves. In 2004, he finished four in the NL MVP voting behind a trio of players having superhero seasons – Barry Bonds, Adrian Beltre, and teammate Albert Pujols. Rolen was also a key part of the Cardinals’ 2006 World Championship team, hitting .421/.476/.737 in the five game victory over the Tigers. When it comes down to Polanco or Rolen, I think the choice here is obvious.

Worst trade: Acquired Mark DeRosa from Indians for Chris Perez and Jess Todd (June 27, 2009)
I’m not an advocate of regretting trading relievers, but I think the Cardinals whiffed with this one. The veteran DeRosa was acquired to stop some of the bleeding at third base due to Troy Glaus’s injury problems (which necessitated Brian Barden, Joe Thurston, and Khalil Greene getting too much playing time), and well…he didn’t do that. In 68 games, DeRosa hit .228/.291/.405 – better than the players he was replacing, but not good by any stretch of the imagination. That winter, he signed a free agent deal with the Giants. Todd didn’t do much of anything in Cleveland, but Perez quickly settled into the closer’s role, made a pair of AL All-Star teams, and saved 124 games over five seasons while pitching to a 3.33 ERA in 267 2/3 innings. He was released this past winter in the face of declining performance and increasing salary, but getting a few solid years from a reliever in exchange for an expendable bench bat is something most teams would absolutely adore.


San Diego Padres
Best trade: Acquired Greg Vaughn and Jerry Parent from Brewers in exchange for Bryce Florie, Marc Newfield, and Ron Villone (July 31, 1996)
In his three year stint with the Padres, Vaughn was pretty damn good. He hit 78 homers, put together a .245/.345/.510 line, and his 1998 All-Star season helped the Padres win the NL pennant. He was then flipped to the Reds as part of package for Reggie Sanders. Both players played well in 1999, but the Padres then flipped Sanders as part of a deal for Ryan Klesko, keeping that gravy train of talent flowing. Villone was the best of the three players that San Diego moved to Milwaukee in this deal, but even he threw just 77 1/3 innings of 3.38 ball for the Brewers before getting traded to Cleveland. Florie had a 4.79 ERA in 94 innings with the Brewers, and Newfield had a .698 OPS in 192 games with his new club.

Worst trade: Acquired Dexter Carter, Aaron Poreda, Clayton Richard, and Adam Russell from White Sox for Jake Peavy (July 31, 2009)
I wish I could lambaste the Padres for the silly Fred McGriff trade (which came just a year early) or shred them for not trading Chase Headley until it was too late, or go off on them for simply not trading Heath Bell at all, but here we are. The Padres kept flip flopping on dealing Peavy, due in part to a no-trade clause that they really didn’t have a desire to make him exercise. Eventually, they relented and moved Peavy to the White Sox. In five years with Chicago, he had a 4.00 ERA, well above the 3.29 mark he posted with the Padres. But while San Diego didn’t necessarily lose out on a lot with Peavy, they didn’t get much of anything back for a guy a year and a half removed from winning the NL Cy Young award. Carter never made the majors and has been out of professional baseball since 2012. Poreda threw 2 1/3 innings with the Padres in 2009, and didn’t make it back to the majors until this season with the Rangers. Russell had a 3.86 ERA in 28 innings with the Padres, was flipped to the Rays as part of the Jason Bartlett trade, and hasn’t made the majors since 2011. The one highlight was Richard, who had a 4.16 ERA over five seasons with the Padres, but had thoracic outlet syndrome surgery this winter, and is still looking for a new employer.


San Francisco Giants
Best trade: Acquired Jason Schmidt and John Vander Wal from Pirates for Armando Rios and Ryan Vogelsong (July 30, 2001)
Oh jeez, this one was a heist. Rios had a .655 OPS in 78 games with the Pirates before getting released. Vogelsong had an ERA of 6.00 in 280 1/3 innings with Pittsburgh before being allowed to walk. Vander Wal was near the end of his career, but was adequate with San Francisco in 2001 before signing with the Yankees. And then, there’s Jason Schmidt. In his six years as a Giant, Schmidt had a 3.36 ERA – a full run lower than the 4.39 mark he posted in his six seasons with the Pirates. Schmidt also made three All-Star teams with the Giants and finished in the top five in NL Cy Young voting twice. It’s crazy how Schmidt somehow turned into an elite, top of the rotation pitcher with the Giants almost immediately after the deal, but with the way things were going for the Pirates at that point in time, it’s not surprising.

Worst trade: Acquired Carlos Beltran from Giants for Zack Wheeler (July 28, 2011)
This wasn’t a bad trade because of Beltran’s performance – he hit .323/.369/.551 in his 44 games with the Giants. However, the Giants ran out of gas after the deal and finished second in the NL West and third in the NL Wild Card race. Beltran signed with the Cardinals after the season, and the Giants ended up winning the 2012 World Series without even needing Beltran. However, the price they paid for this two month rental was steep – their top pitching prospect, Zack Wheeler. Wheeler has shown flashes of brilliance in New York, pitching to a 3.61 ERA in 37 starts with the Mets over the last two seasons. When you look at the unexpected difficulties that the Giants rotation has faced this year past Madison Bumgarner and Tim Lincecum, you’ve gotta wonder how good Wheeler would look in that quintet right about that.


About Joe Lucia

I'm the managing editor of Awful Announcing and the news editor of The Comeback. I also made The Outside Corner a thing for six seasons.